I've setup Squid on windows (Win7) and it works fine, but I want to be able to have the conf files portable. Is it possible for the paths in squid.conf to be relative to the squid working directory rather than absolute?

I'm not sure - but one thing you could consider doing is using an environment variable. Create a %SquidHome% or similar variable and use those in your .conf file. Then if you move it to a new machine you just set the same environment variable to the new install directory.

Unfortunately it doesn't seem to interpret the environment var, just treats it as a string literal :(
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Glenn SlavenSep 13 '10 at 2:50

Ah bummer... Maybe instead you should consider always installing it to the same location? C:\Squid or something like that... so you don't have to fight with it. I doubt it will understand relative paths is why I say this, although you could always try.
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Dave HollandSep 13 '10 at 3:26